Vinyl Acetate → (R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one

Temperature

50 °C

To a solution of vinyl acetate (4.3 g, 50 mmol) in dioxane (63 mL) was added 2-(1-hydroxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Twelve, 2.1 g, 15.1 mmol), and the mixture was heated to 50° C. To the resulting solution was added lipase P30 (0.21 g, 10 wt %) and the heating was continued for 24 h. The reaction mixture was filtered and the filtrate was evaporated to obtain a thick syrupy liquid residue. The residue was purified by flash column chromatography (95:5 dichloromethane:methanol) to give the title compound as a colorless liquid, 0.97 g (92% of theory). 1H NMR (CDCl3, 300 MHz) δ1.61 (d, 3H), 2.20 (s, 3H), 5.65 (q, 1H), 6.35 (d, 1H), 7.97 (d, 1H), 11.94 (s, 1H); [α]D +39.9 (c 1.0, MeOH).

1. customprepared
2. customaccording to the method of Preparation Twelve, 2.1 g, 15.1 mmol), and the mixture
3. additionTo the resulting solution was added lipase
4. filtrationThe reaction mixture was filtered
5. customthe filtrate was evaporated
6. customto obtain a thick syrupy liquid residue
7. customThe residue was purified by flash column chromatography (95:5 dichloromethane:methanol)

ORD record

ord-d33d1572fe8541eab5897a5ab8d479a0

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06414149B1